The question came to mind a while back when I spied a column by Thomas Friedman, who suggested that in our global economy where work gets done cheaper overseas and where, here at home, technology is eating jobs in a rapidly accelerating pace, only the strong will survive. His overall point? Average is officially over.

Your pulse just started racing, right?

Whether or not we happen to be gainfully employed, it’s a message that pushes a button for so many women: We’re convinced that mediocre is never going to cut it, that “average” is something barely north of failure. And in fact, that was the subtext of what many of the women we interviewed for Undecided told us about their struggles with career and life decisions, with second guesses about the road not taken, and with the pervasive belief that today’s women can/should/will have it all: great career, hot sex, well-behaved children, and granite in the kitchen.

Ever wonder how we got to this place?

1. The Treadmill. It starts early and stays late. We’ve written before about young girls building their resumes at their mama’s knee — always with an eye on five years down the road: the right high school, the best soccer team, the prestigious college. It’s a bad habit to break. But what’s worse is that when young girls especially are trained to keep their eye on the prize — we have to take advantage of all those doors that have suddenly flown open, right? — what happens early on is that they become afraid to take risks, to rule things out, for fear that they could fail. Is this future-thinking why I see students who get an assignment back with a “B-plus” on the top — and dissolve into tears? Why “good enough” — never is?

2. We aim to please. Why? We were raised that way — from the days when we were Daddy’s little girl. We talked to an admissions director/counselor at a prestigious girls high school in an affluent area of California, and that’s what she told us she sees in many of the over-achievers in her school. When she talks to students these days, a lot of the chat revolves around serious stress. They admit that a lot is self-induced, but when she asks them, “Well, do you really need to take six honors courses?” the answer will be “But I want to.” What they really want, she suspects, is to please. “Studies show girls have so many more problems than boys— depression, eating disorders, migraines—because girls will stick with the craziness a lot longer than boys will,” she said. “Girls are hard-wired to please, which makes the pressure even bigger. They won’t give up, because to do so would be a failure. And they don’t want anybody to feel they’re a failure, because then they’d be letting people down.”

3. Social Media. Ah, yes. It’s become our own private echo chambers that keeps us comparing and contrasting, the alternate reality where only perfect will do. After all, what else do we see in our news feeds? When was the last time you saw an ugly baby on Facebook? Heard your friend got fired — as opposed to hired? I’ve heard of college girls who have their make-up done before they head out on Friday nights because they want to look good in the pictures that will inevitably appear on Facebook the next day. No joke. And let’s get real: When was the last time you posted anything that was less than, well, cute and witty. Sure, we all know our own online personnas are carefully crafted, that we use them to brand ourselves, but that doesn’t prevent us from looking at all those others out there and believing in the surreality of it all, with the nagging feeling that those folks out there are doing it better, faster, cuter — and having lots more fun.

4. The judge. It’s become a cliche that we tend to judge each other by our choices: Defending what we’ve chosen for our lives—and what we’ve chosen to leave behind. Judging our friends’ choices. Interpreting the fact that our friend has chosen something different as her judgment (and rejection) of what we’ve chosen for ourselves. But what we often forget is that the worst judge of all is often the one in the mirror, holding us to impossible standards and feeding our self doubt. (Be honest here: how many of you sat glued to the tube during the summer Olympics when you were a child, watching those preternaturally small gymnasts — and feeling like you yourself had failed because at the ripe old age of 10 or 12 you had never nailed a vault — and most likely never would?) When we’re deep in the throes of a “Which way should I go,” part of the angst is often the knowledge that no matter what we choose, we will be judged. In all sorts of ways. In ways that men aren’t, and in ways that are often contradictory. And the damnedest truth of all: We often do it to ourselves.

5. The Great Expectations. Especially those that go hand in hand with the mantras with which we’ve been raised: You can do anything! You can do everything! And it will all be amazing! No wonder that the thought of mediocrity sucks our soul. One of our sources who is herself far from mediocre said it best: “I wonder if some of our frustration is about the fact that it’s virtually impossible to excel at everything—wife, writer, teacher, runner, in my case—and so we’re always worried about the area in which we’re not measuring up to our own expectations.”

Sigh. All of which could be the ultimate buzzkill if it weren’t for a bit of wisdom we heard from Swarthmore psychologist Barry Schwartz, author of The Paradox of Choice, who told us about a recent study that found that starting at age 50, people actually get happier. Why? “What you learn from experience,” he told us, “is exactly that good enough is good enough, and once you learn that, you stop torturing yourself looking for the best, and life gets a lot simpler.”